Meyer Lansky (16 episodes, 2015-2016)
Vito Genovese (8 episodes, 2015-2016)
Lucky Luciano (8 episodes, 2015)
Self - Author, The Chicago Outfit (8 episodes, 2016)
Al Capone (8 episodes, 2016)
Tony 'Joe' Accardo (8 episodes, 2016)
Bugs Moran (8 episodes, 2016)
Johnny Torrio (8 episodes, 2016)
Paul Ricca (8 episodes, 2016)
Frank Nitti (8 episodes, 2016)
Dean O'Banion (8 episodes, 2016)
Hymie Weiss (8 episodes, 2016)
Frankie Yale (8 episodes, 2016)
Elliot Ness (8 episodes, 2016)
Sam Giancana (8 episodes, 2016)
Mae Coughlan (8 episodes, 2016)
Frank Capone (8 episodes, 2016)
Ralph Capone (8 episodes, 2016)
Big Jim Colosimo (8 episodes, 2016)
Jimmy Hoffa (8 episodes, 2016)
William Dever (8 episodes, 2016)
Big Bill Thompson (8 episodes, 2016)
Mike D'Angelo / Mike De Angelo (8 episodes, 2016)
Jack McGurn (8 episodes, 2016)
Self / Self - Grandson of Meyer Lansky (8 episodes, 2015-2016)
Narrator (8 episodes, 2015)
Frank Costello (8 episodes, 2015)
Louis 'Lepke' Buchalter (8 episodes, 2015)
Albert Anastasia (8 episodes, 2015)
Genovese's Mobster (8 episodes, 2015)
Detective (8 episodes, 2015)
Self - Former Outfit Associate (7 episodes, 2016)
Self - Author, Capone: The Man and the Era (7 episodes, 2016)
Self - Actor, The Untouchables / Self - Actor, Once Upon a Time in America (7 episodes, 2016)
Benjamin 'Bugsy' Siegel (7 episodes, 2015)
Bootlegger / Thomas Dewey's Associate / Bar Patron / Courtroom Spectator / Juror (7 episodes, 2015)
18th St Gangster / Bootlegger / Senator / Vito Genovese Driver (7 episodes, 2015)
Self - Author, Get Capone (6 episodes, 2016)
Joe Bonanno (6 episodes, 2015)
Self - Author, Paddy Whacked (6 episodes, 2016)
Self - Author, Organized Crime in Chicago (6 episodes, 2016)
Narrator (6 episodes, 2016)
Thomas Dewey (6 episodes, 2015)
Joe Profaci (6 episodes, 2015)
Lucky Luciano's Bodyguard (6 episodes, 2015)
Body Guard (6 episodes, 2015)
Self - Historian (5 episodes, 2016)
Self - Co-author, When Corruption Was King (5 episodes, 2016)
Self - Columnist, Chicago Tribune (5 episodes, 2016)
Carlo Gambino (5 episodes, 2015)
Joseph Valachi (5 episodes, 2015)
Moses Polakoff (5 episodes, 2015)
Anna Genovese (5 episodes, 2015)
Self - Historian, University of Nevada, Las Vegas (4 episodes, 2016)
Self - Former Chicago FBI Chief (4 episodes, 2016)
Self - Former Outfit Associate (4 episodes, 2016)
Jewish Mobster (4 episodes, 2015)
Al Capone (4 episodes, 2015)
Mob Commissioner (4 episodes, 2015)
Tommy Gagliano (4 episodes, 2015)
Self - Chicago History Museum (3 episodes, 2016)
Dewey Assistant / James (3 episodes, 2015)
Cokey Flo (3 episodes, 2015)
Dutch Schultz (3 episodes, 2015)
Tommy Lucchese (3 episodes, 2015)
Pete La Tempa (3 episodes, 2015)
Willie Moretti (3 episodes, 2015)
Self - Grandniece of Al Capone (2 episodes, 2016)
Self - Actor, The Sopranos (2 episodes, 2016)
Self - Author, Kings: The True Story of Chicago's Policy Kings (2 episodes, 2016)
Lead Hitman Who Shot Willie Moretti / Speak Easy Mobster (2 episodes, 2015)
Alice (2 episodes, 2015-2016)
Joe Masseria (2 episodes, 2015)
Gangster in Brothel (2 episodes, 2015)
J Edgar Hoover (2 episodes, 2015)
Vincent Mangano (2 episodes, 2015)
Cop / High Roller (2 episodes, 2015)
Bailiff / Grieving Widower (2 episodes, 2015)
Arnold Rothstein (2 episodes, 2015)
Salvatore Maranzano (2 episodes, 2015)
Dennemora Inmate (2 episodes, 2015)
Older Lucky Luciano (2 episodes, 2015)
Self (2 episodes, 2015)
Igea Lissoni (2 episodes, 2015)
Ralph the Booker (2 episodes, 2015)
Costello Bodyguard / Bootlegger / Bootlegging Accountant (1 episode, 2015)
Senator Estes Kefauver (2 episodes, 2015)
Gangster / Lucky Luciano's Bodyguard (2 episodes, 2015)
Gangster / Masseria's Thug (2 episodes, 2015)
Courtroom Witness / Federal Officer (2 episodes, 2015)
Cigarette Girl (1 episode, 2015)
(2 episodes, 2015)
Self - Author, Sin in the Second City (1 episode, 2016)
Self - Journalist (1 episode, 2016)
George M. Scanlon (1 episode, 2015)
Self - 'Frank Nitti', The Untouchables (1 episode, 2016)
Self - Actor, Goodfellas (1 episode, 2016)
Nucky Johnson (1 episode, 2015)
Grandson of Benjamin 'Bugsy' Siegel / Self (1 episode, 2015)
Self (1 episode, 2015)
Bobby Cee (1 episode, 2015)
Meat Truck Driver (1 episode, 2015)
Meyer Lansky's Book Maker (1 episode, 2015)
Prison Guard (1 episode, 2015)
Phil Mangano (1 episode, 2015)
Galina Orlova (1 episode, 2015)
Young Meyer Lansky (1 episode, 2015)
Old Meyer Lansky (1 episode, 2015)
District Attorney William C. Dodge (1 episode, 2015)
Benito Mussolini (1 episode, 2015)
Angry Businessman (1 episode, 2015)
NY City Detective (1 episode, 2015)
Lucky's Dad (1 episode, 2015)
Funeral Guest (1 episode, 2015)
Lucky's Mother (1 episode, 2015)
Prisoner (1 episode, 2015)
Sandra Lansky (1 episode, 2015)
Jealous Female Patron (1 episode, 2015)
Young Lucky Luciano (1 episode, 2015)
Dr. Richard Hoffman (1 episode, 2015)
Older Vito Genovese (1 episode, 2015)
Ice Pick Victim / Murdered Pedestrian (1 episode, 2015)
Lucky's Sister (1 episode, 2015)
Gambler (1 episode, 2015)
Virginia Hill (1 episode, 2015)
Miguel - Mobster (1 episode, 2015)
Italian Immigrant (1 episode, 2015)
Gangster / Jewish Mobster (1 episode, 2015)
Bartender (1 episode, 2015)
Dutch Schultz Assassin (1 episode, 2015)
Poker Player (1 episode, 2015)
Assassin (1 episode, 2015)
Sheriff (1 episode, 2015)
Vinnie 'The Chin' Gigante (1 episode, 2015)
General Batista (1 episode, 2015)
FBI Agent (1 episode, 2015)
Mulvaney (1 episode, 2015)
Apalachian Mobster (1 episode, 2015)
Abe Reles (1 episode, 2015)
Screaming Prostitute (1 episode, 2015)
Dewey Staffer (1 episode, 2015)
Irishman's Girlfriend / Woman in Speakeasy (2015) (unknown episodes)
Self (unknown episodes)
Italian Immigrant (uncredited) (8 episodes, 2015)
Bystander / Bootleger / Teamster / Bootlegger (uncredited) (6 episodes, 2016)
Al Capone's Body Guard (uncredited) (4 episodes, 2015)
Alberto Anselmi (uncredited) (3 episodes, 2016)
Phyllis McGuire (uncredited) (2 episodes, 2016)
Witness (uncredited) (2 episodes, 2016)
Orange C. Dickey (uncredited) (1 episode, 2015)
Club Patron (uncredited) (1 episode, 2015)
Gunfight Mobster (uncredited) (1 episode, 2015)
Joe Kennedy (uncredited) (1 episode, 2016)
Senate Hearing Chairman (uncredited) (1 episode, 2016)
Anna Torrio (uncredited) (1 episode, 2016)
FBI Agent (uncredited) (1 episode, 2016)
Chicago Tribune Reporter (uncredited) (1 episode, 2016)